Sodium hydride → 1-(2,6-dimethyl-4-nitrophenyl)-4-(trifluoromethyl)-1H-imidazole

HRID 537471Notes

Reaction equation

HRID 537471 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[N:4]=[CH:5][NH:6][CH:7]=1.[H-].[Na+].FC(F)(F)S(O[C:18]1[C:23]([CH3:24])=[CH:22][C:21]([N+:25]([O-:27])=[O:26])=[CH:20][C:19]=1[CH3:28])(=O)=O>CN(C=O)C.O>[CH3:24][C:23]1[CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=[C:19]([CH3:28])[C:18]=1[N:6]1[CH:7]=[C:3]([C:2]([F:9])([F:8])[F:1])[N:4]=[CH:5]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 226621252,6-Dimethyl-4-nitrophenyl trifluoromethanesulfonateHCID 178418921HCID 178418921, compound

Product 1

HCID 681578511-(2,6-dimethyl-4-nitrophenyl)-4-(trifluoromethyl)-1H-imidazoleYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a 0° C. solution of 4-(trifluoromethyl)-1H-imidazole (1.82 g, 13.4 mmol) in DMF (20 mL) was added sodium hydride (0.81 g, 20.1 mmol). The mixture was stirred at room temperature for 1 h. The crude 2,6-dimethyl-4-nitrophenyl trifluoromethanesulfonate prepared above (4.0 g, 13.4 mmol) was added. The mixture was stirred at 80° C. for 12 h. The reaction was diluted with water and extracted with ethyl acetate (30 mL×3). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude material was purified by silica gel chromatography to give 1-(2,6-dimethyl-4-nitrophenyl)-4-(trifluoromethyl)-1H-imidazole (805 mg, 21%) as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 8.01 (s, 2H), 7.47 (s, 1H), 7.23 (s, 1H), 2.11 (s, 6H).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at 80° C. for 12 h
  3. extractionextracted with ethyl acetate (30 mL×3)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-83c0d69484dc4752b365cf7a9e1e9398
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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